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Basic Information
CAS No.: 976-71-6
Name: Canrenone
Article Data: 30
Molecular Structure:
Molecular Structure of 976-71-6 (Canrenone)
Formula: C22H28O3
Molecular Weight: 340.463
Synonyms: 17a-Pregna-4,6-diene-21-carboxylicacid, 17-hydroxy-3-oxo-, g-lactone (6CI,7CI,8CI);17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid g-lactone;17a-(2-Carboxyethyl)-17b-hydroxyandrosta-4,6-dien-3-one lactone;17b-Hydroxy-3-oxopregna-4,6-diene-21-carboxylicacid;20-Spiroxa-4,6-diene-3,21-dione;3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid g-lactone;3'-(3-Oxo-17b-hydroxyandrosta-4,6-dien-17a-yl)-propionic acid lactone;Aldadiene;Phanurane;
EINECS: 213-554-5
Density: 1.19 g/cm3
Melting Point: 158-160 °C
Boiling Point: 541.1 °C at 760 mmHg
Flash Point: 237.6 °C
Solubility: 272.4ug/L(25 oC)
Hazard Symbols: Xn,N
Risk Codes: 40-51/53
Safety: 36/37-61
PSA: 43.37000
LogP: 4.37010
Synthetic route
52-01-7

SPIRONOLACTONE

976-71-6

canrenone

Conditions
ConditionsYield
With mercury dichloride In ethanol Ambient temperature;95%
With sodium methylate In tetrahydrofuran at 20℃; for 18h; Elimination;72%
With potassium dihydrogenphosphate In ethanol at 40℃; Rate constant; Kinetics; Thermodynamic data; var. buffers, pH, temp., ionic strengh, spironolactone and buffer conc.; energy of activation;

potassium canrenoate

976-71-6

canrenone

Conditions
ConditionsYield
With NH2SO4 In methanol for 0.0833333h; Heating;92%
With hydrogenchloride In chloroform for 8h; Heating;86%
With acetic acid for 0.5h; Heating;

17β-hydroxy-3-ethoxy-17α-pregna-3,5-diene-21-carboxylic acid-γ-lactone

976-71-6

canrenone

Conditions
ConditionsYield
With chloranil In methanol; water; 1,2-dichloro-ethane at 20℃; for 1h;84%

17β-hydroxy-3-ethoxy-17α-pregn-3,5-diene-21-carboxylic acid-γ-lactone

976-71-6

canrenone

Conditions
ConditionsYield
Stage #1: 17β-hydroxy-3-ethoxy-17α-pregn-3,5-diene-21-carboxylic acid-γ-lactone With chloranil In methanol; dichloromethane; water at 20℃; for 1h;
Stage #2: With sodium thiosulfate In methanol; water at 20℃; for 1h;
83%
976-70-5

3-oxopregn-4-ene-21,17α-carbolactone

976-71-6

canrenone

Conditions
ConditionsYield
With chloranil In tert-butyl alcohol Heating;70%
With chloranil; toluene-4-sulfonic acid; xylene
52-01-7

SPIRONOLACTONE

A

976-71-6

canrenone

B

79327-11-0

Chloronone

Conditions
ConditionsYield
With mercury dichloride In ethanol for 2h; Heating;A 38%
B 54%
Conditions
ConditionsYield
Yield given. Multistep reaction;
434-03-7

levonorgestrel

976-71-6

canrenone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 98 percent / trimethyl orthoformate, p-toluenesulfonic acid / methanol / 3 h / 50 °C
2: H2, triphenylphosphine, rhodium acetate dimer / ethyl acetate / 20 h / 80 °C / 9000.7 Torr
3: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h
4: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h
5: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating
View Scheme
50407-76-6

17α-ethynyl-17β-hydroxy-5-androsten-3-one ethylene ketal

976-71-6

canrenone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2, triphenylphosphine, rhodium acetate dimer / ethyl acetate / 20 h / 80 °C / 9000.7 Torr
2: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h
3: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h
4: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating
View Scheme
121936-43-4

5'-hydroxyspiro-5-en-3-one

976-71-6

canrenone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / N-methylmorpholine N-oxide (NMO), RuCl2(Ph3P)3 / dimethylformamide / 0.17 h
2: 97 percent / 6 N HCl / tetrahydrofuran / 0.5 h
3: 70 percent / p-chloranil / 2-methyl-propan-2-ol / Heating
View Scheme
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Specification

The CAS registry number of Canrenone is 976-71-6. The IUPAC name is (8R,9S,10R,13S,14S,17R)-10,13-dimethylspiro[2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione. Its EINECS registry number is 213-554-5. In addition, the molecular formula is C22H28O3 and the molecular weight is 340.46. It is a kind of pale yellow to pale green solid and belongs to the classes of Spironolacrone; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. And it is a synthetic pregnadiene compound with anti-aldosterone activity.

Physical properties about this chemical are: (1)ACD/LogP: 2.99; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.99; (4)ACD/LogD (pH 7.4): 2.99; (5)ACD/BCF (pH 5.5): 110.05; (6)ACD/BCF (pH 7.4): 110.05; (7)ACD/KOC (pH 5.5): 1006.86; (8)ACD/KOC (pH 7.4): 1006.86; (9)#H bond acceptors: 3; (10)Polar Surface Area: 43.37 Å2; (11)Index of Refraction: 1.581; (12)Molar Refractivity: 95.22 cm3; (13)Molar Volume: 285.5 cm3; (14)Polarizability: 37.75 ×10-24cm3; (15)Surface Tension: 47.2 dyne/cm; (16)Density: 1.19 g/cm3; (17)Flash Point: 237.6 °C; (18)Enthalpy of Vaporization: 81.89 kJ/mol; (19)Boiling Point: 541.1 °C at 760 mmHg; (20)Vapour Pressure: 8.95E-12 mmHg at 25°C.

Preparation of Canrenone: it can be prepared by potassium canrenoate. This reaction will need reagent NH2SO4 and solvent methanol. The reaction time is 5 minutes by heating. The yield is about 92%.

Canrenone can be prepared by potassium canrenoate

Uses of Canrenone: it can be used to get 6a,7a-Epoxycanrenone. This reaction will need reagents m-chloroperbenzoic acid and 2,6-di-t-butyl-4-methylphenol and solvent CHCl3. The reaction time is 100 minutes by heating. The yield is about 53%.

Canrenone can be used to get 6a,7a-Epoxycanrenone

You can still convert the following datas into molecular structure:
(1)SMILES: O=C5\C=C4\C=C/[C@@H]1[C@H](CC[C@]3([C@H]1CC[C@]32OC(=O)CC2)C)[C@@]4(C)CC5
(2)InChI: InChI=1/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1
(3)InChIKey: UJVLDDZCTMKXJK-WNHSNXHDBD

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral > 5gm/kg (5000mg/kg)   Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 36, 1990.